TrialPay

“I think we had to lay off 70% of the company, and then we eventually turned it around and sold it to Visa”

“And I think I really learned the biggest lesson I learned there was There's of course you build the product. You have to build a product that delights customers that actually delivers value, but you also, your job is also to build belief as a product leader an…”

“So this was kind of the takeaway for me building trial pay is that if you build the boring layer, and I mean boring in the best way possible, then you have almost unlimited optionality because you're the operating system.”

“Thing number one is actually we split the company in two. We had a different product within the company that we just thought was very, very high beta. And there was a lot of controversy around this. I think most people thought that we were idiots for doing thi…”

“Like I viewed this as a colossal failure by me. And if somebody was mad at me, it's like, yeah, they should be mad at me. And I don't hold that against them.”

“We didn't quite hit it just because we had the innovation, but we didn't have the distribution, which is why we sold the visa.”

“There's actually a law in most states, I know this because we tried getting into the insurance lead generation space at TrialPay, where you cannot reward people for switching their insurance.”

“When we did this promotion, it generated about a million dollars in sales for Gap in 24 hours.”

“It took us a long time to get there, but the key thing that caused us to cross the 10,000 merchant barrier was not having individual salespeople, or actually not even buying ads.”

“That would have to go through self-service in order for it to be cost effective.”

“The people that were the least likely to be a channel partner were people that were growing quickly, which kind of makes sense because if you're growing a hundred percent year over year, why would you bother kind of like making a little bit of incremental reve…”

“But also from download.com's perspective, like, if they could make five million dollars a year from real estate that they weren't doing anything with on their site, that's incredibly relevant for them against kind of a shrinking P&L.”

“I mean, in fact, almost all of our competitors went away after we did this deal because it turned from being a very, very vulnerable position where merchants could kind of switch us on or off or like rotate us and five other competitors to one that was a lot m…”

“In those days, I think the Alex I knew would have procrastinated a lot more on starting the company, so I guess we have the H-I-V deadline To thank for, you know, deciding whether or not to move forward with a co-founder.”

“Payments is usually a two-party transaction, and we were adding a third party into that transaction in a way that was beneficial for all three parties.”

“The thinking there was the only way to really get a startup working is to have two separate environments. Right. And I think that was the right decision”

“We basically birthed a Series A startup from Series D TrialPay.”

“I think we're almost 10% of their signups at one point.”

“We would get into an acquisition discussion which I believe happened like 10 times before the ultimate one that worked”

“If we had to do it over again, the way to have potentially built trial pay would have been to say, let's build Stripe first, and then after that gets critical mass, after we have distribution for this thing that is In many respects, a commodity. I mean, I don'…”

“One of the things that I learned at trial pay was that we raised one of our rounds of funding at way too high of a price, and I paid for that because then, guess what, I couldn't, it was hard to sell the company. It was hard to raise money after that”